A nine year deal means that Trout would be selling five of his free agent years. What should those years cost? This is where it gets a little trickier. The recent trend in early career extensions has been to essentially pay something close to current market price for future free agent years. Essentially, teams are buying out future inflation and paying for the right to not have to sign a long term deal that takes a player into his mid-30s, and in exchange for those benefits, the player gets something close to the $6 million per win market rate for their FA years.

Well, that presents a little bit of a dilemma with Trout, because $6 million per win for a +9 WAR player leads to a $54 million per year salary. As good as Trout is, he’s not getting $50+ million per year four years from free agency. [Clayton] Kershaw’s just-signed $215 million extension guaranteed him an average of roughly $32.5 million per year the six free agent years he sold, and while I believe that Trout will beat that AAV, we’re not going to see a leap from $33M to $50M, especially considering their relative proximity to free agency.

But as good and as young as Kershaw is, the reality remains that Trout is significantly better, projecting for roughly +4 WAR per season more than Kershaw going forward. In fact, Trout’s forecasts suggest he is, by himself, as valuable as Kershaw and Freeman put together, and they combined to sell their FA years for pretty close to that $54 million per year mark. While we could put together a reasonable argument that Trout is worth $50M per year for his free agent years, he’s not going to get that; it’s just too far removed from the norms of the day.

As crazy as it sounds, $40 million per year for those five years would actually represent something of a discount, given Trout’s expected production going forward. Even though it’s quite a bit more than Kershaw got, Trout is quite a bit better than Kershaw, and comes with less risk since he isn’t a pitcher. And the separation would be large enough that Trout would likely remain the game’s highest paid player even with future inflation, as that AAV in those years is unlikely to be surpassed any time soon.

If free agent negotiations were like a college class that let you drop your worst exam when computing your final grade, Ubaldo Jimenez would have already signed a very lucrative contract. If 2012 hadn’t happened, he’d probably have been looking at a $100 million deal. Unfortunately for Jimenez, the free agent market doesn’t work like that and he’s likely to get something closer to $30 million or $40 million.

Jimenez had excellent numbers during his time with the Rockies but struggled mightily during his first year and a half in Cleveland before finishing strong in 2013. The team that signs Jimenez is betting on the down year being the blip and the bounce back being the reality, but the uncertainty surrounding that dichotomy is keeping teams at bay. A lot of teams could use Jimenez in his 2013 capacity, but everyone would be wise to avoid him if he’s planning on returning to 2012 form.